Arts and Practices
Boric acid derivatives are known in the art. Boric acid esters are a class of compounds which conform to the following structure; EQU (RO).sub.3 --B
There are a variety of methods of preparation of borate esters. The most common preparative method for boric acid esters is the reaction of boric acid with an alcohol. Low molecular weight alcohols are used in this process. The boric acid ester produced in the greatest quantity is methyl borate, used in the synthesis of sodium borohydride. The utilization relates to the hydrolytic instability of the ester and its reactivity to prepare the borohydride.
The most important references to other methods of preparation of borate esters are as follows;
U.S. Pat. No. 3,454,617 issued in 1969 to Fischer et al discloses a process for the preparation of borate esters of long chain aliphatic alcohols by oxidation of paraffins in the presence of boric acid. This method is not applicable to the compounds of the present invention since the critical guerbet alcohol portion of the molecule cannot be prepared by oxidation of paraffin. Additionally, there is no possibility to include alkylene oxide into the molecule using the Fischer technology.
U.S. Pat. No. 3,660,459 issued in 1972 to Hughes discloses that amino alcohols can be reacted with boric acid to make amino borates which can subsequently converted into quaternary ammonium compounds. These materials are useful as fabric softeners. These compounds are different from the compounds of the present invention in that they utilize amino alcohols, and do not recognize the importance of the guerbet functionality. Additionally, there is no possibility to include alkylene oxide into the molecule using this technology.
U.S. Pat. No. 3,723,495 issued in 1973 to Holtz discloses that unsaturated alcohols can be prepared by the reaction of triolefins with boron compounds followed by hydrolysis. These compounds are different from the compounds of the present invention in that they are alcohols. Not borate esters based upon guerbet alcohols. Additionally, there is no possibility to include alkylene oxide into the molecule using this technology. Borate esters of the prior art hydrolyze easily giving back the starting alcohol. This hydrolytic instability has significantly limited the utilization of these materials in many applications.
Guerbet alcohols, one raw material used in the preparation of the compounds of the present invention, are known to those skilled in the art. Many early patents dealt with the choice of catalyst for the preparation of the beta branched alcohol. Later patents dealt with compounds, compositions and processes which utilize the liquid nature of guerbet derivatives.
Several patents have issued which describe derivatives of guerbet alcohols. None of the patents describe in any way borate esters. All patents use the guerbet alcohol to obtain high molecular weight and liquidity in the products. Typical examples of such patents are;
U.S. Pat. No. 4,425,458 issued in 1984 to Lindner et al teaches that certain guerbet alcohol diesters are useful as plastic lubricants.
U.S. Pat. No. 4,731,190 issued in 1988 and U.S. Pat. No. 4,830,769 both issued to O'Lenick et al, and incorporated herein by reference, teaches that certain guerbet alcohol alkoxylates are useful as metal working lubricants.
U.S. Pat. No. 4,868,236 issued in 1989 to O'Lenick teaches that certain guerbet alcohol citrate esters are useful as plastic lubricants.
U.S. Pat. No. 4,800,077 issued in 1989 to O'Lenick et al, which is incorporated herein by reference, teaches that certain guerbet alcohol based quaternary compounds are useful liquid cosmetic and personal care compounds.
Oil soluble borate esters have been added to aircraft fuel because as they hydrolyze, boric acid results which inhibits the growth of microorganisms.
The compounds of the present invention, unlike other borate esters, are surprisingly stable to hydrolysis, lubricious, non irritating liquids which form films when applied to substrates like skin, hair and textile fibers.